Friday Session-3 – Solution

Friday Session-3 – Solution - Chem 3580 -...

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Chem 3580 - Spring 2010 Friday Session #3 – Feb 12, 2010 - Solution 1. Relative reactivity in nucleophilic aromatic substitution based on our analyses of the carbanion intermediates: Br NO 2 Br NO 2 Br NO 2 Br NO 2 NO 2 Br NO 2 NO 2 > > > > Synthesis (a) Retrosynthesis CH 3 HO OH NH 2 CH 3 HO OH NO 2 Cl HO OH Cl N 2 N 2 Cl Cl Cl O 2 N NO 2 Cl Cl HO OH NO 2 Forward synthesis Cl H 2 SO 4 , ! Cl O 2 N NO 2 HNO 3 Cl H 2 N NH 2 Cl HO OH NO 2 Cl HO OH Cl N 2 N 2 Cl H 2 , Pd/C Cu 2 O Cu(NO 3 ) 2 Cl CH 3 HO OH NO 2 NaNO 2 , HCl 0°C (CH 3 ) 2 CuLi HNO 3 CH 3 COOH Low Temp Cl 2 FeCl 3 H 2 Pd/C CH 3 HO OH NH 2 Alternate CH 3 O 2 N NO 2 CH 3 HO OH NO 2 NaNO 2 , HCl CH 3 HO OH CH 3 N 2 N 2 Cl H 2 , Pd/C Cu 2 O Cu(NO 3 ) 2 Cl 0°C HNO 3 CH 3 COOH Low Temp Highly activated. Can use mild conditions Cl O 2 N NO 2 (CH 3 ) 2 CuLi CH 3 H 2 N NH 2 (b) Retrosynthesis CH 3 O 2 N NH 2 NO 2 CH 3 O 2 N NO 2 Br O 2 N NO 2 O 2 N
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Forward synthesis CH 3 O 2 N NH 2 NO 2 CH 3 O 2 N (NH 4 ) 2 S (CH 3 ) 2 CuLi HNO
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Friday Session-3 – Solution - Chem 3580 -...

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